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Listen, friend. Don't come in hot and buy a strap-on without discussing it beforehand. To increase pleasure you may choose a curved dildo as it will help to stimulate the prostate in a male and if your partner is open to vibration you can certainly opt to get one that vibrates. Pegging isn't always about being the overlord of your boyfriend's ass! And they won't make you feel weird about it. The prostate is your best friend, my dear pegging neophyte.

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People are going totally apeshit over it.

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It looks a little intimidating, but it is literally the luxury car of strap-ons. And they won't make you feel weird about it. Don't go to some creepy, seedy shithole with mannequins wearing leather thongs in plexiglass windows. Conquering your man's backside may be chill for you; but he might be sketched out about you "compromising his manhood" or whatever. It's what dreams are made of. You want to ensure healthy anal penetration and avoid any damage to the anus and rectum. That's it.

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